


Ugly Duckling

by sabstar



Category: Once Upon A Time - Fandom, Once Upon a Time (TV), Once Upon a Time in Wonderland (TV)
Genre: Alternate Universe - High School, F/M, Friendship, beauty pageant
Language: English
Status: In-Progress
Published: 2018-07-05
Updated: 2019-04-21
Packaged: 2019-06-05 19:25:33
Rating: General Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 6
Words: 8,550
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15177647
Author URL: https://archiveofourown.org/users/sabstar/pseuds/sabstar
Summary: Emma Swan is the opposite of a beauty queen. She likes her hair up and her shoes comfortable and couldn’t care less about the Storybrooke Beauty Pageant, run by her mother and former contestant Mary Margret. The pageant happens annually in her town and Emma avoids the mob scene of makeup like the plague. Things start to turn upside down when Emma decides to write an expose for her school newspaper about the superficial scandals that happen within the pageant. Emma may be competing undercover but will she learn that the world of beauty is less superficial and a little more beautiful than she originally thought?





	1. First Day Blues

“Honey, are you sure that’s what you want to wear on the first day of senior year?”, Mary Margaret cautiously asked her daughter, Emma, while simultaneously fiddling with her camera.

Emma looked down at her outfit- slightly ripped black jeans, her beat up pair of white converse, and a faded tee shirt with her favorite band, Pulsing Rebel, on it. Her long blonde hair was sprawled around her shoulders and all she did was add a hint of dry shampoo. There were days that Emma wished her mother could see that what she wore to school was not only her choice, but totally normal.

“It’s just that I bought you those nice wedges, floral dress, and eyeshadow palette…”

“Mom”, Emma interrupted, “this is what I want to wear. And I’m running late.”

Mary Margaret signed and plastered a small smile on her face. 

“Okay honey, if you’re sure. Oh I can’t believe that this is your last first-day-of-school-picture! Time definitely flew by.”

Emma signed and posed for her picture, thinking that this year was going to be exactly the same as the others. Emma tended to sit in the back of class and blend in with the lockers, but she was the editor and head writer of Storybrooke’s High’s newspaper The Mirror- she and her best friend Will Scarlet had named it that because the newspaper reflected the true stories and events over the course of the year. 

That was the best part for Emma. Reality. Dedication to telling the truth. It was the one place in the entire school where Emma could escape the intoxicating superficiality of her classmates, especially around pageant season. 

Mary Margaret ran Storybrooke’s Sweetheart Pageant annually, and each year it got grander and more ridiculous than the last. In Emma’s personal opinion, putting girls onstage to compete against each other and determine their worth based on their waist size was a moral wrong. Also, the fact that “baton twirling” was a talent made her nerves stand on end.

The pageant was a huge deal, and several high school girls claimed to compete in hopes of winning the scholarship money that came with it- but Emma had her suspicions that the true prize was the glittery sash and dazzling 24 karat gold tiara. 

Mary Margret was truly obsessed with the pageant because she won about thirty-five years ago when she was a student at Storybrooke High. She was always telling Emma how it “changed her life” and made her feel special. It was obvious to Emma that she was disappointed she didn’t have a daughter who was interested in the latest fashion trends and school dances. 

“Have a great day sweetie! And remember I’ll be out late tonight finalizing the schedule for this year’s pageant so if you need anything just call.” 

“Thanks Mom. Love you”, Emma said, swinging her dark green backpack over one shoulder and grabbing her car keys.

As Emma backed out of the garage she recited her mantra- one more year of high school and she could finally be free.

Emma’s first stop at Storybrooke High was Mr. Hopper’s classroom at the end of the hall, which also doubled as the newsroom where Emma and Will edited the papers and hung out before class.

“Emma! How was my favorite writer’s summer?,” Mr. Hopper asked when she came through the door.

“You guys know I have ears, right?,” Will Scarlet retorted. 

Emma rolled her eyes but knew how lucky she was to have Will as a friend. His sharp exterior could be coated with sarcasm, but inside he was charming and always willing to help a friend. Freshmen year, when Emma had no one to sit with and was heading towards the library for lunch, Will gave her a place at his table and the two had been best friends ever since. Will tended to write less and focus more on live reporting- he interviewed the actual students about the latest stories while Emma was more comfortable curled up with her blanket and laptop writing until one in the morning.

“You can’t avoid the truth, Scarlet,” Emma said as she walked past Will and took off her signature red leather jacket.

“Hey, I was thinking for our first story of the year we could find out what’s actually in the mystery meat and if it had any correlation with the football team getting food poisoning before Nationals,” Will said, spinning in his chair while throwing up a tennis ball. 

“Interesting idea. Or maybe we could figure out why the drama club is performing Cabaret knowing it’s such a controversial show.”

“Yes! And that’s why you’re the best writer in town!”

Emma giggled and flicked her pencil at Will.

“Ow! Freshly sharpened, Swan? I thought we were friends.”

Archie came back with a stack of Shakespeare plays, since he taught English when he wasn’t helping Emma and Will put the finishing touches on The Mirror.

“Emma, did you finish that article about Killian Jones yet?,” he asked.

Killian Jones- star soccer player and Emma’s crush since sophomore year. He was one of the most popular boys in school and was even on track to be scouted for colleges for his stunning athletic abilities. 

“Um, yeah, I can email it to you during my free period.”

“You know, Emma, maybe you should stop obsessively writing about him and actually talk to him,” Will interrupted, making Emma’s cheeks ignite.

He had a point, Emma knew he did. But going out of her way to flirt with the prom king? No way. Emma thought that she would probably get sick or say the wrong thing and make a big fool of herself. 

“Will, we’ve gone over this before. Killian Jones and I do not mix.”

“You’re never going to know until you try! Just… promise me you’ll think about it? It is our senior year.”

The bell rang, signaling that Emma had to head to Psychology before Mr. Leroy flipped. He was notoriously famous for being grumpy, especially to his first period classes.

“I’ll think about it,” she said, waving goodbye to Will and clenching her notebooks close to her chest.

Maybe this was the year she would actually stop thinking about it and actually do it. 

Emma and Will had survived their first few classes and were heading back from lunch when Emma noticed a bunch of girls crowded around a light pink sign up sheet. 

“Come on, Alice! We have to do it!,” urged Anastasia, the pretty blonde who sat across from Emma in algebra. 

“I’ve been working on my dance routine for this pageant forever,” said Belle, winding a piece of her brunette hair over her finger. 

“It’s our senior year- if we don’t sign up now we never will,” said Elsa as she took out a blue pen and marched forward to the sign up sheet. 

Suddenly Regina Mills appeared, parting the crowd around the pageant list. She examined everyone around her for a second with narrowed eyes and her head held high. Emma knew that she was the Queen Bee- how could you not be when you have gorgeous black hair and a thirst for blood? Regina Mills treated high school like the jungle- she was a lion constantly stalking her prey. She kept tabs on everyone and would even go so far as to post people’s embarrassing secrets to Instagram if they crossed her. Emma stayed away from Regina most of the time, but on her hate account-@QueenR- posted that Will had never been kissed last year. 

She was the scum of the Earth.

Emma watched from a distance as Regina wrote her name in impeccable cursive in a red sparkly pen- almost like the blood of her enemies. She walked slowly away from the list and tripped Will when he and Emma were walking away.

He went down with a crash, half eaten lunch and all, completely mortified that all of the popular girls in his grade had just witnessed that.

“Hey, leave him alone!” Emma said, even surprising herself. She wasn’t one for confrontations, but knew she had to defend her best friend.

“Oops, sorry. It’s just that you two blend in so much I didn’t even see you there.”

She started to walk away and Emma said under her breath, "Whatever Regina. The highlight of your life is going to be winning that dumb pageant.”

“What did you just say Emily?”

Emma winced but decided to stand her ground. She thought she would be scarred by her sharp words and run the other way just like she had done all of high school- but enough was enough.

“It’s Emma. And I said that the best your life is going to get is competing with a bunch of girls you’ve gone to elementary school with over a stupid plastic tiara.”

The small crowd gasped and Will tugged at Emma’s sleeve- signaling that it was best to turn back now. 

“You can think what you want, Emma Swan, but we both know that beauty means power. That crown is mine, and I’d stay out of my way if you know what was good for you, Ugly Duckling.” With those last words Regina snickered and strutted all the way to her next class.

Emma already hated the nickname, Ugly Duckling, that was sure to catch on. Her last name might be Swan but she was no beauty queen.

When Emma and Will got back to the newsroom during last period both of the young journalists were fuming- the victims of the popular kids jokes once again.

“Only one hundred seventy-nine days until we’ll never have to deal with her again,” Will said dismally, staring at the screen of his MacBook. 

“Yep. And then college,” Emma chimed in while stalking Killian Jones’s twitter on her phone.

“I’m sick of taking it, ya know? Regina may have her Instagram account but we have a platform just as powerful- The Mirror. I say we use it to do some good.”

“What are you implying?,” inquired Emma, her eyes darting up from her screen. 

“I saw the way you stood up to her today. I know you think you’re more comfortable behind your laptop screen- but I think you’re skills are so much more than that.”

“Will, I don’t know…”

“Just hear me out! You should become a contestant in the Storybrooke Sweetheart Pageant, write an expose on all the superficial nonsense that goes on, then shove it in Regina’s stupid face!,” he ended triumphantly with a huge smile.

Emma felt her jaw drop. What Will was proposing was completely out of her comfort zone… and besides, she figured it would never work. Emma Swan entering the pageant would be like a three hundred pound dog trying to ice skate.

“Will, that’s crazy. I…”

“No, stop doubting yourself! Since as long as I’ve known you you’ve despised the pageant more than anything. Our society is in shambles until we can look beyond the superficial- you have an opportunity here in Storybrooke to make people see that. This piece could change lives, maybe even stop the contest forever. What do you say?”

Emma chewed on a pencil, her mind racing with all the ways this could go wrong. 

But Will was right- she had an opportunity to expose the pageant for what it really was. She had to take it.

“I’ll do it.”


	2. New Friends

**Summary for the Chapter:**

> Since entering the pageant Emma has gotten a lot of attention- but how long can she keep up the act?

“Emma! Darling!,” Emma heard her mom call as she ran up the stairs to her room on the third floor- her heels clicking every step.

She opened the door breathless and had a huge smile on her face.

“Why didn’t you tell me you were signing up for the pageant, honey?”

She sat on the edge of Emma’s orange and teal bedspread, running a finger across her forehead to sweep her fashionable pixie cut to the side.

Oh, no.

Emma couldn’t tell her mother that she entered the pageant as an undercover contestant to try to destroy the superficial operation from the inside! What was a good lie?

Emma took her time before speaking- blurting out an excuse would only add to her mother’s suspicion.

“I just thought that it might be a nice way to beef up my application for colleges this year. I could really use the scholarship money,” she said, trying not to break eye contact or look insincere. Her mother would never believe that she would willingly enter the pageant without an ulterior motive- no matter how much she wishes it was true. 

“Emma, you’re an honors student who is bound to get some scholarship money without any additional extracurriculars, and up until today you’ve made it very clear that you detest the pageant. Not that I’m complaining, but why are you really doing this?”

Mary Margaret had her cornered. It was time to act. 

Emma started twisting a piece of her long blonde hair around her finger. She had to make this convincing.

“Every year I’ve looked at that stage and all the incredible girls up there- absolutely dazzling in their gowns and” Emma could have gagged at this part,"swimsuits. They have so much talent, beauty, and grace that I was scared to enter because I could never compare! But maybe this is my year and I’m not going to let my insecurities stop me from achieving something that I really, really want.”

Mary Margaret placed a perfectly manicured hand on her heart as delicate tears began to prickle around her soft brown eyes.

“Emma, duckling, I had no idea that you felt that way. I love you and you can win this pageant, sweetheart! It’s a dream come true to hear you’re as passionate about Storybrooke Sweetheart as I am! Don’t worry about a thing- I know exactly how to get you the perfect…”

Emma started to zone out as her mother began listing off the places to get the best dresses, sashes, and hair products. Her mission was successful- her mother completely believed her and, if she played her cards right, she could be a valuable asset in helping Emma get to be in the finals and gain access to the places that could really put her article over the top.

Then why did she feel so rotten?

Emma had never seen her mom as happy and passionate about something as the Storybrooke Sweetheart Pageant- and she could destroy it all. 

Emma shook her head- she couldn’t worry about her mom’s feelings when the greater good would be exposing the pageant for the nightmare it creates for all high school students and the horrible standards it sets for girls.

She just had to ignore the guilt pitting in her stomach.

The next day at school word had spread pretty fast about Emma’s enrollment in the pageant, and for the first time, everyone in school wanted to talk to her. Everyone kept asking her why she signed up, who was going to be her escort, and if she had her dress yet.

Emma kept giving them basic answers- no reason to make anyone suspicious. It was a nice change to feel acknowledged by her classmates, and her entire body felt a lot lighter than before. Instead of pretending to study and silently praying that no one would talk to her she held her head up high and wasn’t afraid to make eye contact with people.

“Dude, you’re like, popular now,” Will said as he and Emma left the lunch line with their trays of hamburgers and soda. 

“I am not popular, Scarlet. People are only intrigued because I’m doing the unexpected,” Emma retorted. 

“Maybe. But at least no one’s putting their dirty socks in your gym locker.”

“Emma!,” a voice called from across the cafeteria. The voice belonged to Elsa, who was waving at Emma to come over to her table. The popular blonde was known for being kind and cool. Emma hated to admit it, but there were many times she was jealous of her friend group and she had avoided Elsa because she made her feel bad.

“Emma, come on,” Will said as he pushed her over to Elsa’s table. 

Emma and Will quickly made their way over to the table where all of Elsa’s friends sat.

There was Belle, one of the smartest girls in their class who was always leading the AP English discussions. Will had tried several times to get up the nerve to ask her to join The Mirror, but ultimately thought that she wouldn’t be interested. Next to Belle was Anastasia, the beautiful blonde bombshell who dominated the cross country team. She always wore bright red lipstick and even designed her own clothes- Emma had seen several of her brilliant creations on Instagram. On the other side of the table was Alice and her boyfriend Cyrus. Alice was the definition of cool because she never really cared what people thought about her. Emma knew that she was a singer who wrote her own songs and performed them at a cute cafe in Storybrooke called The Edge. Her lyrics were open and honest and Cyrus even played guitar for her at performances. Seriously, they were couple goals. Emma knew the least about Cyrus since he was a new student last year, but he seemed to fit in perfectly with the group. On top of playing guitar he was an amazing actor who always got the leads in the school plays. There was even a rumor that he did Sour Patch Kids commercials in England. He had two brothers that also went to school with him, but they weren’t close and didn’t get along, which was surprising to Emma because he was one of the most well-liked guys in the grade. 

“Sit down, we have to talk!,” said Elsa with a friendly smile, scooching over to make room for Emma and Will. 

“Um, about what?” Were they onto her? Did they know that her motives were corrupt for entering the pageant?

“I saw that you signed up for the pageant and we’re all contestants too. We were just wondering if you would like to go dress shopping with us to find the right outfit for the big dance number this weekend.”

Emma was shocked, these girls wanted to hang out with her? The nerdy girl who spends more time with her laptop than actual people?

“Um, yeah sounds good. Thanks!,” said Emma, not able to contain the ghost smile on her lips. 

“Hey, did anyone take Leroy’s psychology test yet?,” asked Anastasia, who was munching on a chicken salad. 

“Oh, yeah, I bombed that. I didn’t really study though,” Cyrus admitted.

“Well you’re no help,” Anastasia said playfully, flicking her marker at him. 

Everything that happened was so natural between them, like they had been friends forever. The group had a certain rhythm and Emma wanted to be part of it. 

“Emma, did you take it yet?,” Alice asked, her hand entertwined with her boyfriend’s.

“Yeah, and don’t worry it’s not rocket science,” she responded.

“Hey maybe you could tutor Cyrus! Trust us, he could use all the help he can get,” Anastasia said.

Emma held her breath- she didn’t her snarky attitude to be the cause of a fight. Instead, to her surprise, the entire group, including Cyrus, started laughing hysterically. 

The rest of the lunch period went by in a blur- and there was more excitement sitting with this group for a twenty minute lunch period than Emma usually got in a day. Belle and Alice were discussing Panic! At the Disco’s new album and the entire group coordinated when they were going to Anastasia’s District Cross Country meet. Will gravitated toward Alice and Cyrus and by the end of lunch the three even had plans to hang out at The Edge after watching Alice’s show. Hanging out with them was like a breath of fresh air, and Emma was happy that Will had made a friend who was a guy.

The rest of the school day was a blur, but the future seemed a lot more bright after being treated like a friend at lunch instead of a target. 

After the last bell rang and Emma had gotten into her car the ignition wouldn’t start. What was going on? Then she realized- she was completely out of gas. It had been getting dangerously low lately- but with all of her focus on the pageant she had forgotten all about it. 

“Hey Emma, you okay?,” a voice called up to her from a beat-up Ford truck. It was Cyrus in the car, with the window rolled all the way down and a concerned look on his face.

“I’m okay, but my car isn’t. I’m completely out of gas and the closest gas station is miles from here.”

“I can give you a ride. Hop in.”

“Really, you don’t mind?”

“Of course not! I’m basically the chauffeur for everyone in the group. Come on,” he said, motioning for her to get in the truck.

Emma knew that she should never get in a car with a stranger, and she had only talked to Cyrus today, but so far he’s shown her nothing but kindness. Also, he implied that she was in the group- she didn’t want to risk that by not accepting a ride. 

When she got in the backseat and turned to give Cyrus her address her heart stopped when she saw who was in the passenger seat.

Killian Jones.

Her life had just turned upside down.

**Notes for the Chapter:**

> Thanks for reading! I always love kudos and comments:)


	3. A Surprising Car Ride

**Summary for the Chapter:**

> Emma finally gets the chance to talk to Killian Jones, and the connection between them is undeniable.

In times of stress Emma always tried to remember her happy place to calm down- which happened to be reading a good Margaret Atwood novel under a shady tree in Central Park. The day she and her parents ventured out of their small town to experience New York City Emma decided that someday she would live there and be a big shot journalist at the Post or Times. That city was like a Mecca to Emma from the stifling small town ways.

However, in this time of stress all Emma could do was forget how to inhale and exhale and worry about dying young of a heart attack.

Killian Jones was in the same car as her. Sitting next to her. Looking at her. 

“Hey,” he said politely, offering a casual and charming smile that Emma had fantasized about for years. 

Emma was too stunned to speak. This was the boy she had been crushing on since sophomore year, who she wrote several articles about, and had stalked on Twitter and Instagram almost every day. It was the equivalent of meeting a celebrity whose music you had listened to on repeat for years, and all Emma could do was nod awkwardly. 

“Hey, Kill, you know Emma right?,” Cyrus asked from the driver's seat. Emma had completely forgotten that he was there. 

“Yeah we had the same homeroom freshmen year. And I can’t believe the stuff she writes about me in the newspaper- she gives me way more credit than I’m due.” 

Emma was stunned that he actually read her work. He knew she existed. It was nice not to feel invisible, to know that you’re hard work was noticed, even just by one person.

“I’m not so sure about that. You’re amazing on the soccer field,” Emma replied. 

Killian let out an easy laugh. “Well, I’m no David Beckham, if you know what I mean.”

Emma laughed, but had no idea who he was referencing. That’s what you get for never having an interest in sports. 

“Cyrus, it’s the second day of senior year, how do you feel?,” asked Killian.

“It’s going good but I’m already missing summer. I’m also kinda bummed it’s our last year together, and that I have zero idea what I’m doing when I get out of here.” 

Emma looked up at the rearview mirror and saw the fear in his eyes. Cyrus wasn’t in any of her honors classes and lived with his mom and two brothers- there probably wasn’t hope for scholarships or a lot of money for school.

“It’ll work out. I haven’t got a plan either,” said Killian, letting out a huff of air as he leaned back into his seat.

“What about soccer?,” Emma asked, surprised that someone as talented as him wouldn’t want to do it his whole life.

“Soccer’s fun, for now, but I think I want to do something more meaningful, you know? Maybe be a marine biologist, or lawyer, or…”

“Killian’s trying to say that he has no idea what he wants to do,” Cyrus interrupted from the driver’s seat. 

“For now. But I do know that it’s not going to be mindlessly playing soccer with no real goal in mind.”

Emma couldn’t believe it- not only did Killian reject the jock stereotype, but he opened up to her. 

“We’re here. See ya later sucker,” said Cyrus to Killian as he pulled up to a nice house with lots of flowers and lawn ornaments strewed around the front yard. 

“Bye Cy, it was nice to meet you Emma,” he said, giving her a quick wink before shouldering his Nike backpack and heading up the cobblestone pathway to his house. 

Emma was still pinching herself, for the first time in her life Killian didn’t seem like a soccer god, just a normal high schooler. And she liked him so much better that way. 

“I drive Killian basically everywhere. He doesn’t really like to talk about it, but his brother Liam died in a car crash when he was ten, and ever since he’s been too afraid to get behind the wheel,” Cyrus said evenly. 

Emma felt a twist in her heart that Killian had to experience that tragedy- if she was in his situation she would be way too traumatized to get her license.

“Thanks,” Emma said, “for trusting me enough to tell me something like that.”

The rest of the ride went great, and Emma and Cyrus actually had a lot in common. They both knew all of the indie bands that no one else had heard of because they weren’t mainstream and Cyrus agreed to be interviewed about the next school play for The Mirror. 

Things were really looking up for Emma Swan- who knew that your car breaking down could lead to a possible romance and a great friend? 

That night Emma started researching the pageant more- she had to know what she was up against. She was not only expected to look perfect all of the time, but had to be steller at the dance routine and have a talent that really shone to move on to the finals and possibly win the competition. Emma wasn’t interested in winning the pageant- but she had to move on to the finals if she wanted to expose the pageant for what it really was. She was going dress shopping with Elsa, Alice, Anastasia, and Belle soon- hopefully they could help her learn some basic dance moves before their first rehearsal next week.

**Notes for the Chapter:**

> Thanks for reading! Sorry this chapter took so long to get up- summer reading definitely to blame! Feel free to leave kudos and comments:)


	4. Beauty Is Not Skin Deep

**Summary for the Chapter:**

> Emma goes dress shopping with her new girl squad and begins to discover the real reason people wear makeup.

Emma Swan knew every corner of Storybrooke like the back of her hand. She had lived there all her life and viewed all of the fading signs and beat up roads like hallmarks of her childhood. The only mom-and-pop store she had never stepped into was Ashley’s Bridal, Storybrooke’s one and only dress store for special events. It was the magical place where every bride-to-be to be got her wedding dress, bridesmaids purchased colorful garments, and where all teenage pageant contestants got their evening gowns. Emma’s mom got her mermaid-style wedding dress at that store and she said she “felt like Cinderella”. Hopefully Emma could have some of that luck for the upcoming pageant. 

The rest of the girls were already at the store, and Emma self consciously pulled her leather jacket closer, even though it was perfectly warm. She didn’t really know a lot about fashion or what was “in” and “out”- what if these girls judged her? 

“Emma! You’re finally here!,” Elsa said, waving her new friend over with a smile.

“Okay, guys, I think I’ve found the one,” said Belle from inside the dressing room.

“Belle, we’ve been here for fifteen minutes, you couldn’t have found the one” exclaimed Alice as she carefully examined all of the light purple gowns. 

Belle suddenly burst out of the dressing room in a hideous orange, hot pink, and neon yellow gown with shoulder pads and a thick zipper in the back. The entire group burst out laughing. 

“I think I’ve won the pageant already,” Belle said, doing lots of ridiculous poses that Anastasia put on her Snapchat story. 

Ashley, the beautiful blonde in charge of Ashley’s Bridal, came over to the girls with a bunch of gowns overflowing in her arms. 

“We still have that in the store? Believe it or not, that’s what girls wore to the prom in the 80’s. But you make it work!,” she said, putting the dresses on a spare chair.

“Thanks Ashley,” Anastasia said. “I work here part time, so I know where all of the best outfits are stored,” she told Emma with a wink. 

Emma was so grateful to be hanging out with these girls. They shone with confidence, wit, and could really make her laugh. Will would always be her best friend, but it never hurt to have a girl squad. 

“Okay, so I found these in all of your signature colors that are in everyone’s price range with Anastasia’s employee discount,” Ashley continued. She handed Anastasia a tight bright red gown that complemented her perfectly. Belle looked gorgeous in a pale yellow two piece with a skirt that flared out at the bottom. Elsa got an icy blue dress with an open back and a long train that showed all of her beautiful curves. Alice finally settled on a pale purple gown with intricate beading and a bedazzled v-neckline. The only one who hadn’t found the perfect dress yet was Emma. 

Anastasia looked her over and chewed on her bottom lip in concentration. “I can really see you rocking navy. How do you feel about prints?,” she asked, excitement dancing in her eyes. She was truly passionate about fashion. Emma used to think that dresses and designs were pointless- but maybe she was wrong if it brought her friend so much joy. 

“I’m all for it, whatever you think would look good,” Emma said, trusting Ana’s fashion expertise. 

“I have the perfect dress for you! I’ve only designed it in my sketchbook but I can sew it for you before the pageant! Imagine a gown with a solid navy top with a high neckline and a printed skirt of ivory and navy flowers. I have all of the fabric and I know that I could make it great,” Ana said, her eyes practically begging Emma to let her take on this challenge. 

“That would be amazing. But only if you want to,” Emma said, not wanting to force her friend into a project that was bound to be a lot of work. 

“Yes, I definitely want to! Your dress is going to be a showstopper!,” Ana said, giving Emma a quick hug. 

After all of the girls made their purchases they said goodbye to Ashley- who said that she was rooting for them this pageant season. 

 

After shopping Elsa, Emma, Belle, Alice, and Anastasia went to The Edge for lunch. Since Alice performed there every Friday and weekend she convinced the owner to give them pink lemonades for free. 

Emma felt so accepted by these kind girls, and a little embarrassed that she had judged them so much and pushed them away because of her envy. 

“So Cyrus told me your car broke down and he had to give you a ride, that sucks,” Alice said through sips of her lemonade. 

“It wasn’t that bad. I actually got to talk to Killian Jones for the first time,” Emma said. 

“We’ve gone to school with him since third grade and you only spoke to him yesterday?,” Belle asked, unintentionally calling out Emma. 

“Yeah, I guess. It’s kinda strange since I’ve written articles about him every year, but I never had the nerve to actually talk to him.”

The entire group looked around at each other- it was obvious that she had a crush on soccer superstar Killian Jones. 

“Well, Kill is a great guy. Maybe he could even be your pageant escort,” Elsa said with a quick wink. The group definitely didn’t miss how Emma’s cheeks flushed pink. 

The waiter came with their chips and guacamole and the entire group moved on to talking about different things going on at school. There was the track meet, auditions for the school musical, and the endless amount of AP work they had to suffer until graduation. Emma started to forget that she was on a mission. She couldn’t allow herself to forget her true motives for the pageant no matter how fun it was hanging out with these girls. 

“So for the pageant I was thinking I’ll do a liquid winged eyeliner with a matte lip and fill in my eyebrows to the max,” Anastasia said, popping another chip into her mouth. 

To be a journalist she couldn’t be too quick to form an opinion- maybe instead of assuming all makeup is bad she should understand why people wear it. 

“Anastasia, why do you wear makeup all of the time?,” Emma asked, trying to sound casual. She had to get to the root of the problem. 

Emma could tell that this question had been surprising for her, hopefully she hadn’t offended her new friend. 

“Well… I like makeup because it makes me more confident. I can control how I look and present myself to the world. I love it when my lips are bright red and my eyes are coated in sparkly shadow. When I look in the mirror I see me. However, I hate how advertisements for hair dye and different concealers have people look like they are super happy because of the makeup. Happiness can’t be bought in a bottle. My happiness comes from knowing that I can look how I want and do what I want, makeup for me is freedom and control. Makeup is art and I like to wear it- but that doesn’t mean that other women who don’t wear it are not beautiful or confident.”

“I agree,” added Alice. “I almost never wear makeup but society wants to say that it’s an obligation. Or that there is a price tag on beauty. But that’s not true! All girls should be encouraged to wear what they are most confident in whether it’s sweatpants, jeans and a tank top, or a sparkly dress. As long as we are happy and confident who cares what beauty products it takes for us to get there?” 

Emma felt another weightlifting from her shoulders. Women don’t need to hold themselves to stereotypes- style is about being confident in your individuality. It’s as simple as that. All a girl needs to wear is what makes her happy on the inside- and that could be achieved wearing makeup or not. 

This revelation was making Emma’s head spin. She had wasted so much time in high school judging girls based on what products they put on their faces instead of understanding that what they wanted to wear was a choice just as much as her decision to reject all makeup.

As the group of girls left The Edge and promised to see Emma at lunch on Monday she felt empowered. Beauty was however you defined it- not a set of rules that said girls were pretty if they had the smallest nose, longest legs, or skinniest waist. Beauty was not skin deep.

**Notes for the Chapter:**

> Thanks for reading! I always love kudos and comments:)


	5. Pageant Escort

**Summary for the Chapter:**

> Will Emma have the guts to ask Killian Jones to be her escort to the Storybrooke Sweetheart Pageant?

“What’s on your face?,” asked Will as Emma came up to him at the lockers in the morning. 

“Will, that is so rude. All I’m wearing is a tiny bit of mascara and blush, it’s not like I am a completely different human being.”

“Um, sure, okay. How did dress shopping go? Did you get any dirt?”

Emma winced at his question, just like every time she remembered that her intentions were not pure for entering the pageant and joining her girl group. 

“I don’t want to get dirt on Elsa, Belle, Alice, or Ana. I only want it on the institution of the pageant itself.”

“Not even on Regina?”

“Hmm… I guess I can make an exception for Her Majesty.” With that Emma and Will both burst into laughter. 

“I still can’t believe we’re really doing this! It’s going to be the best issue yet. There’s one big problem though, you have no talent.”

“Really Scarlet?,” Emma said, rolling her eyes at her best friend.

“Come on Swan don’t take it as an insult! You’re gifted but you can’t exactly go onstage and write on your laptop. We need a plan. Didn’t you use to do dance?”

“If by dance you mean my mother physically forced me to attend ballet lessons in the first grade, then yes.”

“Um, can you draw?”

“There’s a reason I’m a writer, Will. This is hopeless!”

“Don’t worry, we’ll think of something. It just needs to be fast. Anyway, can I ask you a question?”

That was strange, Will was usually anything but indirect and never got nervous around his best friend- what was going on? 

“Of course. Shoot,” Emma replied, her mind reeling with all of the possibilities of what could be bothering him. His grade was slowly sinking in pre-calc, and college applications were due soon, but Will never got jittery about that kind of stuff. 

“Um, okay, here goes. I just wanted to ask you… you know, if you’re comfortable saying… if Ana might be interested in me. As more then friends. And maybe if she might be… you know… cool with me being her escort to the pageant.” 

“Will, you like Ana?”

Will didn’t even have to respond, his face was turning a deeper shade of red by the second. 

“Yes, Swan, I’m crazy about her! Cyrus keeps telling me we would be a perfect match, but every time I see her I sweat uncontrollably and I forget every word in the English language! You have to help me, could you ask her if she likes me too?”

“Will, you and Ana would be a perfect match! She would be so lucky to have you, but I think you should ask her to be her escort yourself.” 

“You just saw how nervous I got asking you to ask her, and we’ve been best friends since middle school! If I start asking her I’m going to choke and say the wrong thing, and then die of embarrassment. It’s just like you and Killian.” 

“Actually, I have talked to Killian Jones. And none of the things I worried about happened. I’m actually more embarrassed it took me so long to say anything to him.”

Will’s jaw was dropped, and it looked like his eyes were bugging out of his sockets. 

“You talked to him? Killian Jones? Star soccer player? The person you have been crushing on for years?”

“It’s hard to believe, but yes, it happened.”

“No bloody way. The world has turned upside down.”

“My car broke down the other day, so Cyrus gave me a ride, and I didn’t know Killian would be there too. But we started talking and now I realize how ridiculous it was that I didn’t have the guts to it before.”

“What are you saying?”

“I’m saying that I was a coward. I should have had the nerve to talk to him, and when I did none of my fears came true. So man up and talk to Ana! And if you don’t you’ll always regret it.”

Will looked at her in defeat, knowing what he had to do. 

“Why do you always have to be so bloody stubborn?,” he said lovingly, hiking his backpack up on his shoulder as they walked to class in sync. “I’ll do it- I’ll ask her out. But only if you ask Killian.”

“Ask him what?”

“Ask him to be your escort,” Will said with a wink before he ducked into his next class. 

Emma knew Will was being a good friend and could read between the lines. He knew Emma would want him to be with Ana, and that she wanted to be with Killian. But the only way she would actually make a move was if his happiness was on the line too. What are friends for?

 

Emma had decided that asking Killian to be her escort to the pageant had to happen fast, or she would never have the nerve to do it. Emma was under no grand delusions that Killian would actually want to be with her, and she was bracing herself for the certain rejection. It would be like ripping off a bandaid- painful, but fast and over before she knew it. Then things could go back to normal. 

At lunch Emma couldn’t stop fiddling with her fingers, feeling like the world was shattering around her. She knew that none of her friends knew about her plans to ask Killian to be her escort, also known as her impending doom, but it seemed like a betrayal at how casually Alice and Cyrus were competitively playing a game on their phones, or how Belle was trying to warn Ana about the material on next period’s science test. To ask Killian to the pageant she had to walk over to his side of the cafeteria, with all of the sweaty jocks and swarming queen bees. Then, the worst part of all, she had to actually ask him. How would she even say it? Could she form words around him all of the time, or did that only happen once by some miracle? 

“Emma, are you okay? You look a little on edge,” Elsa observed, looking worried as she re-braided her icy blonde hair.

“Yeah, yeah, I’m cool. I mean, I’m okay.”

“Are you sure? Because you haven’t eaten any of your sandwich,” Belle chimed in, starting to get worried about her friend. 

“I’m fine I just have to… do something,” Emma said, immediately getting up from her seat and heading to Killian’s table. 

Her feet felt like lead, and she could not stop sweating. She didn’t know how she was going to ask him, maybe Will would believe she asked him if she just walked walked over there and casually chatted about the weather. Just as she was about to turn back, worried she didn't think it through, Regina stepped in her way. 

“What are you doing here, Ugly Duckling?,” she asked, raising a perfect brow as she blocked Emma from Killian’s direction. 

“I just came to… uh…” Emma fumbled. 

“Spit it out Swan! Or get back to your side,” she said, smiling menacingly with her set of perfectly bleached teeth. 

“Regina, just, get out of my way,” Emma said, walking around her as fast as she could. She had almost reached his table, just a few more steps to go before she heard Regina come after her. 

“You can’t just walk away from me…,” she started, but stopped when she saw Killian wave at Emma, beckoning her over. 

“Emma! I was hoping I would see you around!,” he said, chewing on an apple with a smile on his face. 

“Um, thanks! I just wanted to say…” Emma started, before she realized Regina was right behind her. 

“You two know each other?,” she asked, flabbergasted.

“Yeah, of course- we’re friends,” Killian replied, giving Emma a wink. 

Emma wondered if this was what a heart attack felt like. She couldn’t handle the amount of adrenaline and dopamine Killian Jones pumped into her system with just one look. 

Regina slowly walked back to her friends, but Emma had a feeling they were more like minions who would immediately start plotting to destroy her. 

“Regina can be so annoying sometimes. So, what did you want to talk about?,” Killian asked again, looking up at her with his big brown eyes. 

Don’t turn back, Emma told herself. You’ve already made it this far. 

“I want to know if you’ll be my escort for the pageant. If you don’t want to, I understand, but it might be fun. I know that pageants are dumb and stupid and stuff but…”

“Emma, I would love to go with you!,” he said, his face brightening by the second. “I was kinda hoping you’d ask.”

Emma was shocked. Killian Jones was her pageant escort, and it was not a dream. 

“Here’s my number,” he said, scribbling his digits on a piece of notebook paper. “Text me.”

Emma knew that she only got a phone number, but it felt like the golden ticket to Willie Wonka’s Chocolate Factory. 

“I will. And thank you so much for saying yes, it means a lot.”

“Of course. I’m excited about it,” Killian said, his smile never fading for a second.

“Me too! I guess… I’ll see you around?,” Emma said, glancing back to her table, where even Alice and Cyrus had looked up from their video game to see what all the fuss was about. 

“Emma Swan, you will definitely be seeing me around.”

 

When Emma walked back to her table everyone was staring at her in shock.

“What were you doing over there?,” Ana asked. 

“If Regina got in your way one more time I was going to kick her ass,” Alice chimed in. 

“What were you and Killian talking about?,” Cyrus asked. 

“Well, I just asked him to be my pageant escort. And he said yes,” Emma said, hoping it wasn’t noticeable how much she blushed. 

Everyone around the table burst into excited chatter, but the person most happy to hear the news was Will. Maybe love was in the air at Storybooke High.

**Notes for the Chapter:**

> Thanks for reading! It's been a long time since I've updated and this is well overdue, but I hope you enjoyed! P.S. positive comments fuel my soul:)


	6. Spontaneous

**Summary for the Chapter:**

> When Emma finally texts Killian for the first time, can friendship become something more?

It was Friday night and Emma was relaxing in her room as per usual while her favorite Spotify station played low from her speakers. Last week had been crazy, and Emma still could not believe that she had Killian’s number. She had tried so many times to summon the courage to text him, but kept chickening out. What was she supposed to say? What if she said the wrong thing or used the wrong emoji? 

Emma knew that she had to text him tonight- it had been four days and she didn’t want him to think she was ghosting him. She just had to say something. Anything. 

She flopped on her teal and white colored bedspread and punched his number into her phone. With a shaky breath she texted HEY- IT’S EMMA and pressed send. 

She had to distract herself- if not she would go crazy waiting for a response, so she started working on her senior thesis. Every student was required to write one to graduate, and while most students blew it off until the last minute Emma really wanted to impress Mr. Hopper. Usually Emma was bursting with ideas for new projects, English was her forte after all, but this time she was drawing a blank. When her phone buzzed next to her Emma jumped, not expecting Killian to respond so fast. 

HEY! WHAT’S UP? he responded. 

Emma: NOT MUCH, HBU? 

Killian: JUST CHILLING AT HOME, TEXTING A GIRL I REALLY LIKE. 

Emma gasped, Killian liked her? Romantically? This was all happening way too fast. It was best to just ignore it, Emma wanted Killian but she was not prepared for this level of flirting. 

Emma: SAME HERE, BUT I THOUGHT SOCCER JOCKS WERE SUPPOSED TO BE AT PARTIES 24/7

Killian: LOL, NOT REALLY. SOME OF THE GUYS ON MY TEAM GO OUT EVERY WEEKEND BUT I WOULD RATHER STAY IN AND WATCH MOVIES, EVEN IF THAT MAKES ME A TOTAL NERD

Emma: THAT DOES NOT MAKE YOU A TOTAL NERD. BEING A TOTAL NERD IS WORKING ON YOUR SENIOR THESIS THIS EARLY IN THE YEAR ON A FRIDAY NIGHT. 

Killian: IS THAT WHAT YOU’RE DOING? 

Emma: UNFORTUNATELY 

Killian: WELL, SINCE WE ARE BOTH NOT DOING ANYTHING, WOULD YOU WANNA GO OUT AND GET SOME PIZZA, THERE IS THIS REALLY GOOD PLACE RIGHT NEAR MY HOUSE

Emma’s jaw dropped. Killian was so spontaneous he wanted to go out with her? Without any plans made beforehand? 

Emma was totally freaking out, so she Facetimed Will, he would know what to do.

Will picked up on the third ring. 

“Hey Swan! I’m at work right now so we can’t talk for that long but what’s up?,” he asked. Will worked at Granny’s, the cute popular diner in Storybooke. Last summer when he and Emma were out getting breakfast he thought his car was in drive when it was actually in reverse and he crashed into the side of Granny’s. Since Granny, the sweet elderly lady who ran the diner, was old school she let Will work off his debt as a waiter and busboy instead of pressing charges. That meant that most nights Will was serving his sentence, doing his best to remember how many shots of vanilla people wanted in their lattes or what kinds of pancakes people ordered. 

“Okay, so Killian just asked me to go out and get pizza with him. Tonight.”

“That’s great, you should go!”

“Will, I am so not ready for this! I don’t know what to say or how I should dress or…”

“Stop worrying so much! This is your dream guy, you should be over the moon.”

“I’m just nervous, I don’t want him to not like me anymore.”

Will sighed and ran a free hand down his face. 

“Emma Swan, you owe it to yourself to go on that date and see what happens with Killian. Don’t worry so much, if he doesn’t like you for you then he isn’t worth it and at least you know you gave it a try.”

“But….”

“Oh no, Granny’s coming this way. Just go on the date and text me all the details later. Bye!”

Will immediately hung up, but his encouraging words meant the world to Emma and gave her the confidence boost she definitely needed. She picked up her phone and texted Killian. 

Emma: YEAH, LET’S DO IT. WHERE SHOULD WE MEET? 

Emma burst out laughing when Killian sent her a gif of someone happy dancing. 

Killian: ITS CALLED LEROY’S BRICK OVEN PIZZA, NOT TOO FAR FROM SCHOOL. MEET AT 8? 

Emma: SOUNDS GOOD. SEE YOU THEN

Killian: SEE YA :-) 

Emma had exactly one hour to get ready, so she decided on a simple white dress with a paint-splattered denim jacket on top and her converse. She tied her long blond hair into a high pony and added a little dry shampoo. To complete the look she defined her lashes with the new mascara Ana had encouraged her to buy and added a little lip gloss. 

“Hey Mom, I’m going out- be back at ten!,” Emma called to Mary Margret as she raced in her car before her mom started asking her embarrassing questions about Killian. She typed Leroy’s Brick Oven Pizza into her GPS and started driving. 

As she pulled into the parking lot she checked her phone and got a text from Killian saying he was already there. 

Here goes nothing, Emma thought to herself as she entered the pizza place.

**Author's Note:**

> Thanks for reading! Although the show has ended I've been toying with this idea for a while and finally wanted to share it:) Feel free to leave kudos and comments!


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